Asking Better Questions

If you’re not getting what you want, you might not be asking the right way.

It’s an easy trap to fall into. It’s easy to ask, but it’s not so easy to ask well. It takes practice. Even with practice, I still fall into the traps of asking too generic a question, or asking the wrong person. However, I catch myself faster, and it’s easy to course correct, because I know what asking intelligently looks like.

It looks simple right? That’s the beauty. The challenge is to apply it. For example, when you ask specifically, really figure out what you need. A way to do this is to figure out, what do you need somebody to do. What’s the action?

When it comes to asking somebody who can help you, find somebody who has actually solved the problem you have, or has the resources to help you. It’s fun to share problems with friends, but if you need results, check that you’re asking who can actually help.

People help those who help themselves. They also help people who bring something to the table … a game of "tradesies." They also want to know what’s in it for them. If you can create value, so it’s not just one-way, you up level your game, and create the win-win.

Show a little conviction. If you’re waffling in what you want, then it’s hard for people to sign-up to help. Ask with focus, and believe in what you ask for.

Keep asking until you get what you want. But don’t keep asking the same way if it’s not working. Change your approach. Maybe you need to ask a different question. maybe you need to ask a different person. Maybe you need to find a more valuable proposition.

5 COMMENTS

I agree with these key points. We are only wasting our breath if we ask someone who doesn’t know or can’t help us. Many will speculate and give us a good guess, but for a definitive answer we need to go to the right source.

It reminds me of when I’m doing online research. I will go from site to site until I find the one that answers my question.

Online research still surprises me. As much stuff as I can find online, I’m surprised by how many of the great needles are still in offline haystacks. But like you say, we need to go to the right source.

And what if it makes absolutely no difference to them if your problem goes unsolved? So there’s no ‘tradesies’ because the thing they need most from you is that you stop asking and go away.

That’s the part I’m stuck on (in a very practical, real world way).

If the only person or body with the resources/power/expertise to solve your problem doesn’t want to help then you’re felled at the first hurdle. Or probably even before. There’s no negotiating, no logic, no wiggle room.

I’d seriously appreciate an answer/advice because this is an actual, current issue for me.

@ Sam — If there’s no difference in whether your problem gets unsolved, then there’s no skin in the game — so you have to ask, why are you dependent on them. That might open additional options to you, including how you frame the problem, and which solutions you bet on (I tend to force myself to find 3 options, and then test each path.)

First, I try never to limit myself to a single point of failure. Even when there is absolutely the right person for the job, or the right person to help, it’s rare that the stars align.

Second, I try to make sure that if I do have a dependency, that I remove it or mitigate the risk, as quickly as possible.

If somebody won’t help, I try to make sure at least they won’t hurt.

Most importantly though, I try to find why they won’t help. Is it because there is nothing in it for them, or because they are against the idea, or against me. If I don’t know their concerns, I can’t address them, so I make sure i know their concerns. I need to be able to articulate why they won’t help. The test is, would they agree, with my articulation?

I also make it as easy as possible for them to help me. If I truly need their help, then I make it as painless as possible for them, and find as much value or opportunity for them as I can create. Sometimes this is just reframing the problem. Sometimes it’s just connecting at values. Sometimes, it means I “owe them one.”

It also depends on context. I optimize for collaboration, finding 3rd alternatives, and influence without authority. Sometimes collaboration won’t work for a variety of reasons. Sometimes co-ercion is the right answer. Sometimes, failure, or losing the battle, is the best answer. Sometimes the best way to get help is to use the system around that person to make it in their best interest to help (such as if their manager makes it a priority, or it’s a shared goal or commitment, etc.)

Two great books on the strategy and tactics are Get the People on Your Side, and Influence without Authority.

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